Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers

Leumann, Christian (2003). Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers. Organic letters, 5(11), pp. 1987-1990. American Chemical Society

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A fluorinated OPA monomer containing the base thymine ((Z)-t-F-OPA) was synthesized in 12 steps, featuring a highly selective allylic over homoallylic Mitsunobu substitution for the introduction of the nucleobase. F-OPA modified PNA decamers were prepared by the MMTr/acyl protection strategy. The thermal stability of duplexes of PNA decamers containing (Z)-t-F-OPA units with antiparallel complementary DNA was measured. We found a strong dependence of stability from the sequential position of the (Z)-t-F-OPA units, ranging from ¢Tm of +2.4 to -8.1 °C/modification relative to unmodified PNA.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Leumann, Christian

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

1523-7060

Publisher:

American Chemical Society

Language:

English

Submitter:

Marcel Hollenstein

Date Deposited:

23 Apr 2015 12:47

Last Modified:

23 Apr 2015 12:47

URI:

https://boris.unibe.ch/id/eprint/67218

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